This invention relates to a novel 5-iodo-4-phenethylaminopyrimidine derivative useful as agricultural and horticultural pesticides, a novel 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine which is a preparation intermediate thereof, processes for producing these compounds and agricultural and horticultural pesticides.
Some 4,5-dihalogeno-6-(xcex1-substituted ethyl)pyrimidines useful as an intermediate for medicines or agricultural chemicals have been known (for example, Japanese Provisional Patent Publication No. 320141/1993, etc.). However, 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine in which the 5-position of the pyrimidine ring is substituted by an iodine atom as in the present invention has not yet been disclosed.
Moreover, as a 4-phenethylaminopyrimidine derivative which is similar to the present invention, there is Japanese Provisional Patent PublicationNo. 258223/1995. However, the 4-phenethylaminopyrimidine derivative in which the 5-position of the pyrimidine ring is substituted by an iodine atom has not been disclosed.
Accordingly, the 5-iodo-4-phenethylaminopyrimidine derivative of the present invention would be a novel compound is a novel compound and it has been not known to have agricultural and horticultural pesticidal activities.
An object of the present invention is to provide a novel 5-iodo-4-phenethylaminopyrimidine derivative, its process for producing the same, and an agricultural and horticultural pesticide containing the same as an effective ingredient.
Another object of the present invention is to provide a novel 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine which is useful as an intermediate for medicines and agricultural chemicals.
The present inventors have studied to solve the above-mentioned problems, and as a result, they have found that a novel 5-iodo-4-phenethylaminopyrimidine has remarkable agricultural and horticultural insecticidal, acaricidal, nematocidal and fungicidal activities whereby they have accomplished the present invention.
Also, the present inventors have also studied to solve the above-mentioned problems, and as a result, they have found a process for producing a novel 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine, whereby they have accomplished the present invention.
That is, the present invention is as mentioned below.
The first invention relates to a 5-iodo-4-phenethylaminopyrimidine derivative represented by the following formula (1): 
wherein R1 represents a halogen atom, an acyloxy group having 2 to 4 carbon atoms or a hydroxyl group; R2 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms;
n is an integer of 1 to 3; and * represents an asymmetric carbon atom.
The second invention relates to a process for producing the 5-iodo-4-phenethylaminopyrimidine derivative represented by the above-mentioned formula (1) which comprises allowing a pyrimidine represented by the following formula (2): 
wherein R1 and * have the same meanings as defined above, to react with a phenethylamine represented by the following formula (3): 
wherein R2 and n have the same meanings as defined above.
The third invention relates to a 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine represented by the following formula (2): 
wherein R1 and * have the same meanings as defined above.
The fourth invention relates to a process for producing 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine represented by the following formula (2-1): 
wherein R3 represents a chlorine atom or a bromine atom and * has the same meaning as defined above, which comprises allowing a pyrimidine represented by the following formula (4): 
to react with a halogen represented by the following formula (5):
(R3)2 xe2x80x83xe2x80x83(5) 
wherein R3 has the same meaning as defined above.
The fifth invention relates to a process for producing a 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine represented by the following formula (2-2): 
wherein R4 represents an acyloxy group having 2 to 4 carbon atoms, and * has the same meaning as defined above, which comprises allowing the pyrimidine represented by the following formula (2-1): 
wherein R3 and * have the same meanings as defined above, to react with a lower aliphatic acid represented by the following formula (6):
R4xe2x80x94H xe2x80x83xe2x80x83(6) 
wherein R4 has the same meaning as defined above.
The sixth invention relates to a process for producing a 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine represented 
by the following formula (2-3):
wherein * has the same meaning as defined above, which comprises allowing the pyrimidine represented by the following formula (2-2): 
wherein R4 and * have the same meanings as defined above, to react with an inorganic base represented by the following formula (7):
Mxe2x80x94OH xe2x80x83xe2x80x83(7) 
wherein M represents an alkali metal.
The seventh invention relates to a process for producing a 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine represented by the following formula (2-4): 
wherein * has the same meaning as defined above, which comprises allowing the pyrimidine represented by the following formula (2-3): 
wherein * has the same meaning as defined above, to react with a fluorinating agent represented by the following formula (8): 
The eighth invention relates to agricultural and horticultural pesticides containing the 5-iodo-4-phenethylaminopyrimidine represented by the above-mentioned formula (1) as an effective ingredient.
In the following, the present invention is explained in detail.
Various kinds of the substituents mentioned in the above respective compounds are as follows.
(R1)
R1 represents a halogen atom, an acyloxy group having 2 to 4 carbon atoms or a hydroxyl group.
As the halogen atom, there may be mentioned a chlorine atom, an iodine atom, a bromine atom, a fluorine atom, etc.; and preferably a chlorine atom and a fluorine atom.
As the acyloxy group having 2 to 4 carbon atom, there may be mentioned those having a straight or branched alkyl group; preferably an acetyloxy group.
(R2)
R2 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms.
As the halogen atom in R2, there may be mentioned a chlorine atom, an iodine atom, a bromine atom, a fluorine atom, etc.; and preferably a chlorine atom and a fluorine atom.
As the alkyl group having 1 to 4 carbon atoms, there may be mentioned a straight or branched alkyl group; and preferably a methyl group.
As the haloalkyl group having 1 to 4 carbon atoms, there may be mentioned a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2-fluoroethyl group, etc., and preferably a trifluoromethyl group.
As the alkoxy group having 1 to 4 carbon atoms, there may be mentioned a straight or branched one, and preferably a methoxy group.
As the haloalkoxy group having 1 to 4 carbon atoms, there may be mentioned a difluoromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2-fluoroethoxy group, etc., and more preferably a trifluoromethoxy group and a 2,2,2-trifluoroethoxy group.
(n)
n is an integer of 1 to 3; and preferably 1 or 2.
The compounds (1) of the present invention have an amino group so that an acid addition salt derived therefrom is also included in the present invention.
As an acid which forms an acid addition salt, there may be mentioned, for example, an inorganic acid such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, etc.; a carboxylic acid such as formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, aconitic acid, etc.; a sulfonic acid such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.; saccharine, etc.
Also, the compounds (1) or (2) of the present invention contain asymmetric carbon atom represented by * so that the respective optical isomers, racemic isomers or mixture thereof derived therefrom are each included in the present invention.
As the compounds (1) , those in which the above-mentioned various substituents are combined may be mentioned, and those preferred in view of chemical effects are as follows.
(1) Compound (1) in which R1 is a halogen atom and R2is a hydrogen atom.
(2) Compound (1) in which R1 and R2 are halogen atoms and n is 1.
(3) Compound (1) in which R1 is an acyloxy group having 2 to 4 carbon atoms and R2 is a hydrogen atom.
(4) Compound (1) in which R1 is a halogen atom, R2 is an alkyl group having 1 to 4 carbon atoms and n is 1.
(5) Compound (1) in which R1 is a halogen atom, R2is an alkoxy group having 1 to 4 carbon atoms and n is 1.
(6) Compound (1) in which R1 is a halogen atom, R2is a haloalkoxy group having 1 to 4 carbon atoms and n is 1.
Also, as the compound (2) which is a synthetic intermediate of the above-mentioned compound (1), those having the substituent preferred as R1 mentioned above may be mentioned.
(Synthetic method of Compound (1))
As a preferred process for producing the 5-iodo-4-phenethylaminopyrimidine derivative represented by the above-mentioned formula (1), there may be mentioned, in addition to Synthetic method 1 described as the second invention, the following four kinds of production processes (Synthetic methods 2 to 5).
(Synthetic method 2)
A process for producing a 5-iodo-4-phenethylaminopyrimidine derivative (referred to as Compound (1-2)) represented by the following formula (1-2): 
wherein R2, n and * have the same meanings as defined above and R4 represents a lower acyloxy group, which comprises allowing a 4-phenethylaminopyrimidine derivative (referred to as Compound (1-1)) represented by the following formula (1-1): 
wherein R2, n and * have the same meanings as defined above and R3 represents a chlorine atom or a bromine atom, to react with a lower aliphatic carboxylic acid represented by the following formula (6):
R4xe2x80x94H xe2x80x83xe2x80x83(6) 
wherein R4 has the same meaning as defined above.
(Synthetic method 3)
A process for producing a 5-iodo-4-phenethylaminopyrimidine derivative (referred to as Compound (1-3)) represented by the following formula (1-3): 
wherein R2, n and * have the same meanings as defined above, which comprises allowing the 4-phenethylaminopyrimidine derivative (referred to as Compound (1-2)) represented by the above formula (1-2) to react with an inorganic base represented by the following formula (7):
Mxe2x80x94OH xe2x80x83xe2x80x83(7) 
wherein M represents an alkali metal.
(Synthetic method 4)
A process for producing a 5-iodo-4-phenethylaminopyrimidine derivative (referred to as Compound (1-4)) represented by the following formula (1-4): 
wherein R2, n and * have the same meanings as defined above, which comprises allowing the 4-phenethylaminopyrimidine derivative (referred to as Compound (1-3)) represented by the above formula (1-3) to react with a fluorinating agent (diethylaminosulfur trifluoride: DAST) represented by the following formula (8): 
(Synthetic method 5)
A process for producing the 5-iodo-4-phenethylaminopyrimidine derivative (referred to as Compound (1-4)) represented by the above formula (1-4), which comprises allowing the 4-phenethylaminopyrimidine derivative (referred to as Compound (1-1)) represented by the following formula (1-1): 
wherein R2, R3, n and * have the same meanings as defined above, to react with a compound represented by the following formula (9):
Mxe2x80x94F xe2x80x83xe2x80x83(9) 
wherein M has the same meaning as defined above.
The above-mentioned Synthetic methods 1 to 5 of the compounds (1) according to the present invention are described in more detail.
(Synthetic method 1)
Synthetic method 1 is a method in which Compound (2) and Compound (3) are reacted in a solvent in the presence of a base to obtain Compound (1).
As a kind of the solvent, it is not particularly limited so long as it does not directly participate in the present reaction, and there may be mentioned, for example, a chlorinated or not chlorinated aromatic, aliphatic or alicyclic hydrocarbon such as benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, chloroform, dichloroethane, trichloroethylene, etc.; an ether such as tetrahydrofuran, dioxane, diethyl ether, etc.; a nitrile such as acetonitrile, propionitrile, etc.; a ketone such as acetone, methyl ethyl ketone, etc.; an aprotic polar solvent such as N,N-dimethylformamide, dimethylsulfoxide, sulforane, N,N-dimethylimidazolidinone, N-methylpyrrolidone, etc.; and a mixture of the above-mentioned solvents.
With regard to an amount of the solvent, it may be used so that Compound (2) becomes 5 to 80% by weight; and preferably 10 to 70% by weight.
As a kind of the base, it is not specifically limited, and there may be mentioned organic and inorganic bases, for example, a tertiary amine such as triethylamine, an organic base such as DBU, an inorganic base such as a hydride, hydroxide, carbonate, hydrogen carbonate of an alkali metal and alkaline earth metal; and preferably an organic base such as triethylamine.
An amount of the base to be used is 1 to 5-fold mole based on Compound (2); preferably 1.2 to 2.0-fold mole.
A reaction temperature is not specifically limited, and it is within the temperature range from a room temperature to a boiling point or less of the solvent to be used; preferably 60 to 110xc2x0 C.
A reaction time may vary depending on the above-mentioned concentration and temperature; and generally 0.5 to 5 hours.
An amount of the starting compounds to be used is 1.0 to 5-fold mol of Compound (3) based on the amount of Compound (2); and 1 to 1.1-fold mol is preferred.
Compound (2) to be used in the present invention can be prepared by the method shown in the following scheme. 
wherein R3, R4, M and * have the same meanings as defined above; and DAST represents diethylaminosulfur trifluoride.
Compound (4) can be produced by the method shown in the following scheme according to the method described in, for example, Journal of Chemical Society (JCS) pp. 3478-3481 (1955). 
With regard to the synthesis of Compound (2-4) from Compound (4), it is described in detail below (Synthetic methods 6 to9).
As Compound (3), a commercially available product may be used or it may be produced according to the method shown below. 
wherein R2 and n have the same meanings as defined above.
The desired compound (1) produced as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Synthetic method 2)
Synthetic method 2 is a method of obtaining Compound (1-2) (a compound in which R1 in the compound (1) is an acyloxy group having 2 to 4 carbon atoms) by reacting Compound (1-1) and Compound (4) in a solvent.
As a kind of the solvent, there may be mentioned an ether, a ketone as described in Synthetic method 1, an amide such as N,N-dimethylacetamide; 1,3-dimethyl-2-imidazolidone, sulforane, dimethylsulfoxide; and a mixture of the above-mentioned solvents; and preferably N,N-dimethylformamide of amides.
An amount of the solvent may be set in such an amount that Compound (1-1) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
As a kind of a base, there may be mentioned an inorganic base mentioned in Synthetic method 1; preferably potassium carbonate.
An amount of the base to be used is 1 to 5-fold mol based on the amount of Compound (1-1), preferably 2 to 5-fold mol.
A reaction temperature is not specifically limited, and is within the temperature range of room temperature to a boiling point of the solvent to be used or less; preferably 60 to 100xc2x0 C.
A reaction time may vary depending on the above-mentioned concentration and temperature; and generally 0.5 to 8 hours.
As Compound (4), a commercially available product may be used.
The desired Compound (1-2) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Synthetic method 3)
Synthetic method 3 is a method of obtaining Compound (1-3) by reacting Compound (1-2) and Compound (5) in a solvent.
As a kind of the solvent, there may be mentioned an ether, a ketone, an amide as described in Synthetic method 1; an alcohol (methanol, ethanol, propanol, butanol, etc.); water; and a mixture of the above-mentioned solvents; and preferably a mixture of an alcohol (methanol, ethanol) and water.
An amount of the solvent may be set in such an amount that Compound (1-2) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
As Compound (5), there may be mentioned inorganic bases mentioned in Synthetic method 1 which are commercially available products; preferably sodium hydroxide and potassium hydroxide.
An amount of the base to be used is 1 to 2-fold mol based on the amount of Compound (1-2), preferably 1 to 1.5-fold mol.
A reaction temperature is within the temperature range of 0xc2x0 C. to room temperature; preferably room temperature.
A reaction time may vary depending on the above-mentioned concentration and temperature; and generally 0.5 to 3 hours.
The desired Compound (1-3) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Synthetic method 4)
Synthetic method 4 is a method of obtaining Compound (1-4) by reacting Compound (1-3) and Compound (6) in a solvent or without solvent.
As a kind of the solvent, there may be mentioned a chlorinated or not chlorinated aromatic, aliphatic or alicyclic hydrocarbon or an ether as described in Synthetic method 1; and preferably a chlorinated aliphatic hydrocarbon such as dichloromethane.
An amount of the solvent may be set in such an amount that Compound (1-3) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
A reaction temperature is not specifically limited, and is within the temperature range of room temperature to a boiling point or less of the solvent to be used; preferably 0xc2x0 C. to room temperature.
A reaction time may vary depending on the above-mentioned concentration and temperature; and generally 0.5 to 3 hours.
As Compound (6), it is not specifically limited; and the above-mentioned diethylaminosulfur trifluoride (DAST) which is a commercially available product is preferred.
An amount of Compound (6) to be used is 1 to 2-fold mol based on the amount of Compound (1-3), preferably 1 to 1.5-fold mol.
The desired Compound (1-4) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Synthetic method 5)
Synthetic method 5 is a method of obtaining Compound (1-4) by reacting Compound (1-1) and Compound (7) in a solvent.
As a kind of the solvent, there may be mentioned an amide such as N,N-dimethylformamide, N,N-dimethylacetamide; 1,3-dimethyl-2-imidazolidone, sulforane, dimethylsulfoxide; and a mixture of the above-mentioned solvents.
An amount of the solvent may be set in such an amount that Compound (1-4) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
A reaction temperature is within the temperature range of room temperature to a boiling point or less of the solvent to be used; preferably 100 to 120xc2x0 C.
A reaction time may vary depending on the above-mentioned concentration and temperature; and generally 1 to 15 hours.
As Compound (7), there may be mentioned potassium fluoride, sodium fluoride, cesium fluoride which are commercially available products; preferably potassium fluoride and cesium fluoride.
An amount of Compound (7) to be used is 1 to 5-fold mol based on the amount of Compound (1-1), preferably 1 to 3-fold mol.
The desired Compound (1-4) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
Next, a method for preparing 4-chloro-5-iodo-6-(xcex1-substituted ethyl)pyrimidine which is a synthetic intermediate of the present invention is explained below.
(Synthetic method 6)
Synthetic method 6 is a method of obtaining Compound (2-1) by reacting Compound (4) and Compound (5) in a solvent.
As a kind of the solvent, it is not specifically limited so long as it does not directly participate in the present reaction, and there may be mentioned, for example, a chlorinated or not chlorinated aromatic, aliphatic or alicyclic hydrocarbon such as benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, chloroform, dichloromethane, dichloroethane, trichloroethylene, etc.; an ether such as tetrahydrofuran, dioxane, diethyl ether, etc.; and a mixture of the above-mentioned solvents; and preferably a chlorinated aliphatic hydrocarbon such as chloroform, dichloromethane and dichloroethane.
An amount of the solvent may be set in such an amount that Compound (4) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
A reaction temperature is not particularly limited and is within the temperature range of room temperature to a boiling point or less of the solvent to be used; preferably 10 to 30xc2x0 C.
A reaction time may vary depending on the above-mentioned concentration and temperature; and generally 0.5 to 5 hours.
Amounts of the starting materials to be used are 1.0 to 5-fold mol of Compound (5) based on the amount of Compound (4), preferably 1 to 1.3-fold mol.
Compound (4) to be used in the present invention can be produced, as mentioned above, by the method described in, for example, Journal of Chemical Society (JCS), pp. 3478-3481 (1955).
The desired Compound (2-1) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Synthetic method 7)
Synthetic method 7 is a method of obtaining Compound (2-2) (a compound in which R1 in Compound (2) is an acyloxy group having 2 to 4 carbon atoms) by reacting Compound (2-1) and Compound (6) in a solvent in the presence of a base.
As a kind of the solvent, there may be mentioned an ether, a ketone, an amide such as N,N-dimethylacetamide; 1,3-dimethyl-2-imidazolidone, sulforane, dimethylsulfoxide; and a mixture of the above-mentioned solvents; and preferably N,N-dimethylformamide of the amide.
An amount of the solvent may be set in such an amount that Compound (2-1) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
As a kind of the base, it is not specifically limited, and there may be mentioned an organic and inorganic base, for example, organic bases including a tertiary amine such as triethylamine, and DBU; and inorganic bases such as a hydride, hydroxide, carbonate, hydrogen carbonate of an alkali metal or an alkaline earth metal, etc.; preferably potassium carbonate of the inorganic base.
An amount of the base to be used is 1- to 5-fold mol based on the amount of Compound (2-1); preferably 2- to 5-fold mol.
A reaction temperature is not specifically limited and is within the temperature range of room temperature to a boiling point or less of the solvent to be used; preferably 50 to 100xc2x0 C.
A reaction time may vary depending on the above-mentioned concentration and temperature; and is 0.5 to 8 hours.
As Compound (6), a commercially available product may be used.
The desired Compound (2-2) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Synthetic method 8)
Synthetic method 8 is a method of obtaining Compound (2-3) by reacting Compound (2-2) and Compound (7) in a solvent.
As a kind of the solvent, there may be mentioned an alcohol such as methanol, ethanol, propanol, butanol, etc.; a nitrile such as acetonitrile, propionitrile, etc.; a ketone such as acetone, methyl ethyl ketone, etc.; an aprotic polar solvent such as N,N-dimethylformamide, dimethylsulfoxide, sulforane, N,N-dimethylimidazolidinone, N-methylpyrrolidone, etc., water; and a mixture of the above-mentioned solvents; and preferably a mixture of an alcohol (methanol, ethanol) and water.
An amount of the solvent may be set in such an amount that Compound (2-2) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
As Compound (7), there may be mentioned an inorganic base such as sodium hydroxide and potassium hydroxide; preferably sodium hydroxide.
An amount of Compound (7) to be used is 1 to 2-fold mol based on the amount of Compound (2-2), preferably 1 to 1.5-fold mol.
A reaction temperature is within the temperature range of 0xc2x0 C. to a boiling point or less of the solvent to be used; preferably room temperature to 50xc2x0 C.
A reaction time may vary depending on the above-mentioned concentration and temperature; and is 0.5 to 3 hours.
The desired Compound (2-3) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Synthetic method 9)
Synthetic method 9 is a method of obtaining Compound (2-4) by reacting Compound (2-3) and Compound (8) in a solvent or without solvent.
As a kind of the solvent, there may be mentioned a chlorinated or not chlorinated aromatic, aliphatic or alicyclic hydrocarbon, and an ether; and preferably dichloromethane which is a chlorinated aliphatic hydrocarbon.
An amount of the solvent may be set in such an amount that Compound (2-3) becomes 5 to 80% by weight; preferably 10 to 70% by weight.
A reaction temperature is not specifically limited and is within the temperature range of 0xc2x0 C. to a boiling point or less of the solvent to be used; preferably 0xc2x0 C. to room temperature.
A reaction time may vary depending on the above-mentioned concentration and temperature; and is 0.5 to 1 hour.
As Compound (8), it is not specifically limited; and preferably diethylaminosulfur trifluoride (DAST) which is a commercially available product as mentioned above.
An amount of Compound (8) to be used is 1 to 2-fold mol based on the amount of Compound (2-3), preferably 1 to 1.5-fold mol.
The desired Compound (2-4) prepared as mentioned above may be subjected to usual post-treatment such as extraction, concentration, filtration, etc., after the reaction, and, if necessary, may be subjected to purification by the known methods such as recrystallization, various kinds of chromatographies, etc.
(Prevention effects)
As the agricultural and horticultural noxious organisms on which a controlling effect by the compound (I) of the present invention can be observed, there may be mentioned agricultural and horticultural noxious insects (e.g. Hemiptera (planthoppers, leafhoppers, aphides, whiteflies, etc.), Lepidoptera (cabbage armyworms, diamond-back moth, leafroller moths, pyralid moths, common cabbage worm, etc.), Coleoptera (Tenebrionid beetles, leafbeetles, weevils, scarabs, etc.), Acarina (citrus red mite, two-spotted spider mite, etc. of Tetranychidae family, pink citrus rust mite of Eriophyidae family, etc.)), nematodes (e.g. root knot nematodes, cystcid nematodes, root lesion nematodes, white-tip nematodes, pine wood nematodes), bulb mite in soil, hygienically noxious insects (e.g. flies, mosquitoes, cockroaches, etc.), noxious insects of stored grains (e.g. rust-red flour beetles, bean weevils, etc..), wood insects (e.g. termite such as formosan subterranean termite, Reticulitermes speratus and Cryptotermes domesticus; powderpost beetles, drugstore beetles, carpenter moths, long-horned beetle, bark beetles, etc.) and also agricultural and horticultural diseases (e.g. wheat brown rust, barley powdery mildew, cucumber downy mildew, rice blast, tomato late blight, etc.).
(Agricultural and horticultural fungicide)
The agricultural and horticultural fungicide of the present invention has particularly remarkable in insecticidal, acaricidal and nematocidal effects, and contains one kind or more of Compound (1) as an effective ingredient.
Compound (1) may be used singly, but usually, it is preferred to formulate a carrier, surfactant, dispersant, auxiliary, etc. (for example, it is prepared as a composition such as dust powder, an emulsifiable concentrate, a fine granule, a granule, a wettable powder, an oily suspension, an aerosol, etc.) according to the conventionally known method.
As the carrier, there may be mentioned, for example, a solid carrier such as bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, calcium hydroxide, siliceous sand, ammonium sulfate, urea, etc., a liquid carrier such as hydrocarbon (kerosine, mineral oil, etc.), aromatic hydrocarbon, (benzene, toluene, xylene, etc.), chlorinated hydrocarbon (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethyleneglycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanone, ethylene glycol, etc.), polar solvent (dimethylformamide, dimethylsulfoxide, etc.), water, etc.; a gas carrier such as air, nitrogen, a carbonic acid gas, fleone, etc. (in this case, mixture spreading can be carried out), and the like.
As the surfactant and dispersant which can be used for improving attachment of the present chemical to and absorption thereof in animals and plants, and improving characteristics such as dispersion, emulsification and spreading of the chemical, there may be mentioned, for example, alcohol sulfates, alkylsulfonate, lignosulfonate and polyoxyethylene glycol ether. Further, for improving properties of its formulation, for example, carboxymethyl cellulose, polyethylene glycol and gum arabic can be used as an auxiliary.
In preparation of the present chemical, the above carrier, surfactant, dispersant and auxiliary can be used singly or in a suitable combination, respectively, depending on the respective purposes.
When the compound (I) of the present invention is made into formulations, the concentration of the active ingredient is generally 1 to 50% by weight in an emulsifiable concentrate, generally 0.3 to 25% by weight in a dustable powder, generally 1 to 90% by weight in a wettable powder, generally 0.5 to 5% by weight in a granule, generally 0.5 to 5% by weight in an oily suspension, and generally 0.1 to 5% by weight in an aerosol.
These formulations can be provided for various uses by diluting them to have a suitable concentration and spraying them to stems and leaves of plants, soil and paddy field surface, or by applying them directly thereto, depending on the purposes.